4-(3-aminobenzoyl)-5-cyclopropylisoxazoles effective as herbicides

ABSTRACT

4-(3-Aminobenzoyl)-5-cyclopropylisoxazoles of the formula (I) are described as herbicides. 
     
       
         
         
             
             
         
       
     
     In this formula (I), A, X, Y and Z are radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen.

4-(3-Aminobenzoyl)-5-cyclopropylisoxazoles effective as herbicides

The invention relates to the technical field of the herbicides, in particular to that of the herbicides for the selective control of broad-leafed leaves and grass weeds in crops of useful plants.

It has already been disclosed in various publications that certain benzoylisoxazoles have herbicidal properties. Thus, EP 0 418 175, EP 0 527 036 and WO 97/30037 describe benzoylisoxazoles which are substituted on the phenyl ring by a variety of radicals.

However, the compounds known from these publications frequently do not display a sufficient herbicidal activity. It is therefore an object of the present invention to provide herbicidally active compounds whose herbicidal properties are improved over those of the compounds known from the prior art.

It has now been found that certain 4-benzoylisoxazoles which have a cyclopropyl group attached in the 5-position and whose phenyl ring has an amino or amidine group attached in the 3-position are especially suitable as herbicides.

The present invention relates to 4-(3-aminobenzoyl)-5-cyclopropylisoxazoles of the formula (I) or their salts

in which

-   A is NR¹R² or N═CR³NR⁴R⁵, -   R¹ and R² independently of one another are hydrogen, (C₁-C₆)-alkyl,     (C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,     (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where the     six abovementioned radicals are substituted by m halogen atoms, -   R³, R⁴ and R⁵ independently of one another are hydrogen,     (C₁-C₆)-alkyl or (C₃-C₆)-cycloalkyl, where the three last-mentioned     radicals are substituted by m halogen atoms, -   X and Y independently of one another are hydrogen, (C₁-C₆)-alkyl,     (C₁-C₄)-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,     (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,     (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, halogen,     (C₁-C₄)-alkyl-S(O)_(n), (C₃-C₆)-cycloalkyl-S(O)_(n), nitro or cyano, -   Z is hydrogen or CO₂R⁶, -   R⁶ is (C₁-C₆)-alkyl or (C₃-C₆)-cycloalkyl, -   m is 0,1, 2, 3, 4 or 5, -   n is 0, 1 or 2.

In formula (I) and all formula given below, alkyl radicals which have more than two carbon atoms may be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.

If a group is polysubstituted by radicals, this is to be understood as meaning that this group is substituted by one or more of the abovementioned radicals which are identical or different.

Depending on the nature and linkage of the substituents, the compounds of the formula (I) may be present in the form of stereoisomers. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Equally, stereoisomers occur when n is 1 (sulfoxides). Stereoisomers can be obtained from the mixtures generated in the course of the preparation by customary separation methods, for example by chromatographic separation methods. Equally, stereoisomers can be prepared selectively using stereoselective reactions and employing optically active starting materials and/or adjuvants. The invention also relates to all stereoisomers and their mixtures which are comprised by the formula (I), but are not specifically defined.

Preferred compounds of the formula (I) are those in which

-   A is NR¹R² or N═CR³NR⁴R⁵, -   R¹ and R² independently of one another are hydrogen, (C₁-C₆)-alkyl,     (C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₃-C₆)-cycloalkyl or     (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, -   R³, R⁴, R⁵ independently of one another are hydrogen or     (C₁-C₆)-alkyl, -   X and Y independently of one another are methyl, methoxy,     trifluoromethyl, chlorine, bromine, fluorine or methylsulfonyl, -   Z is hydrogen or CO₂R⁶, -   R⁶ is methyl or ethyl.

Especially preferred compounds of the formula (I) are those in which

-   A is NR¹R² or N═CR³NR⁴R⁵, -   R¹ and R² independently of one another are hydrogen, methyl, ethyl,     propyl, methoxyethyl, ethoxyethyl or methoxypropyl, -   R³, R⁴, R⁵ independently of one another are hydrogen or methyl, -   X and Y independently of one another are methyl, methoxy,     trifluoromethyl, chlorine, bromine, fluorine or methylsulfonyl, -   Z is hydrogen or CO₂R⁶, -   R⁶ is methyl or ethyl.

Unless otherwise defined, the substituents and symbols in all the formulae mentioned hereinbelow have the same meaning as described in formula (I).

For example, compounds according to the invention in which Z is hydrogen can be prepared by the method specified in Scheme 1 and known from EP 0 418 175 A1 by reacting a compound of the formula (II) with a salt of hydroxylamine, such as hydroxylamine hydrochloride, in a suitable solvent such as ethanol or acetonitrile, if appropriate with catalysis of a base such as triethylamine, at a temperature of from room temperature up to the temperature of the boiling point of the solvent. In formula (II), L is a group such as ethoxy or dimethylamino.

Compounds of the formula (II) can be prepared for example by the method specified in Scheme 2 and in J. Heterocyclic Chem., 1976, 13, 973 by reacting the dione (III) with, for example, triethyl orthoformate with acid catalysis.

The preparation of compounds of the formula (Ill) is known to the skilled worker in principle and can be effected for example with trisubstituted benzoic acids of the formula (IV) or their derivatives such as acid chloride or ester. For example, such benzoic acids of the formula (IV) can be prepared by the methods described in WO 98/42678.

Compounds according to the invention in which Z is hydrogen or CO₂R⁶ can be prepared for example by the method specified in Scheme 3 and known from WO 97/30037 by reacting a compound of the formula (IIa) with hydroxylamine or a salt thereof in a suitable solvent such as ethanol or acetonitrile, if appropriate with catalysis of a base such as triethylamine, at a temperature of from room temperature up to the temperature of the boiling point of the solvent.

Compounds according to the invention in which Z is CO₂R⁶ can also be prepared for example by the method specified in Scheme 4 and known from WO 98/5153 by reacting a compound of the formula (III) with a 2-chloro-2-hydroxyiminoacetic ester of the formula (V).

Compounds of the formulae (II) and (IIa) in which X, Y, A and Z are defined as for formula (I) and L is defined as mentioned above are novel and also subject matter of the present application.

Collections of compounds of the formula (I) and/or their salts which can be synthetized in accordance with the abovementioned reactions can also be prepared in a parallelized manner, which can be effected manually or in a partly or fully automated manner. Here, it is possible for example to automate the procedure of the reaction, the work-up or the purification of the products or intermediates. In total, this is understood as meaning the procedure as described for example by D. Tiebes in Combinatorial Chemistry—Synthesis, Analysis, Screening (Editor Günther Jung), Wiley 1999, on pages 1 to 34.

A series of commercially available apparatuses can be used for the parallelized reaction procedure and work-up, for example Calpyso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA, or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 11 3AZ, England or MultiPROBE Automated Workstations from Perkin Elmar, Waltham, Mass. 02451, USA. Chromatographic apparatuses, for example from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA, are available, inter alia, for the parallelized purification of compounds of the formula (I) and their salts or of intermediates generated in the course of the preparation.

The apparatuses listed lead to a modular procedure in which the individual passes are automated, but manual operations must be carried out between the passes. This can be circumvened by the use of partly or fully integrated automation systems, where the relevant automation modules are operated by, for example, robots. Such automation systems can be obtained for example from Caliper, Hopkinton, Mass. 01748, USA.

The performance of individual, or a plurality of, synthesis steps can be aided by the use of polymer-supported reagents/scavenger resins. The specialist literature describes a series of experimental protocols, for example in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

Besides the methods described herein, the preparation of compounds of the formula (I) and their salts can be effected fully or in part by solid-phase-supported methods. For this purpose, individual intermediates, or all intermediates, of the synthesis or of a synthesis adapted to the relevant procedure are bound to a synthesis resin. Solid-phase-supported synthesis methods are described sufficiently in the specialist literature, for example Barry A. Bunin in “The Combinatorial Index”, Academic Press, 1998 and Combinatorial Chemistry—Synthesis, Analysis, Screening (Editor Günther Jung), Wiley, 1999. The use of solid-phase-supported synthesis methods permits a series of protocols known from the literature, which, again, can be carried out manually or in an automated manner. For example, the reactions can be carried out by means of IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, Calif. 92064, USA.

Carrying out individual or a plurality of synthesis steps, both on a solid and in the liquid phase, can be aided by the use of microwave technology. A series of experimental protocols are described in the specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (Editors C. O. Kappe and A. Stadler), Wiley, 2005.

The preparation in accordance with the processes described herein generates compounds of the formula (I) and their salts in the form of substance collections, which are referred to as libraries. The present invention also relates to libraries which comprise at least two compounds of the formula (I) and their salts.

The compounds of the formula (I) according to the invention (and/or their salts), hereinbelow together referred to as “compounds according to the invention”, have an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants. The active substances also act efficiently on perennial harmful plants which produce shoots from rhizomes, woodstocks or other perennial organs and which are difficult to control.

The present invention therefore also relates to a method of controlling undesired plants or for regulating the growth of plants, preferably in crops of plants, where one or more compound(s) according to the invention is/are applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), to the seeds (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or to the area on which the plants grow (for example the area under cultivation). In this context, the compounds according to the invention can be applied for example pre-planting (if appropriate also by incorporation into the soil), pre-emergence or post-emergence. Examples of individual representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention shall be mentioned, without the mention being intended as a limitation to certain species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

If the compounds according to the invention are applied to the soil surface before germination, either the emergence of the weed seedlings is prevented completely or the weeds grow until they have reached the cotyledon stage, but then stop their growth and, finally, die completely after three to four weeks have elapsed.

When the active substances are applied post-emergence to the green plant parts, growth stops after the treatment, and the harmful plants remain in the growth stage of the time of application or die fully after a certain period of time, so that competition by weeds, which is harmful to the crop plants, is thus eliminated at an early point in time and in a sustained manner.

Although the compounds according to the invention display an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, are damaged only to an insignificant extent, or not at all, depending on the structure of the respective compound according to the invention and its application rate. This is why the present compounds are highly suitable for the selective control of undesired plant growth in plant crops such as agriculturally useful plants or ornamentals.

Moreover, the compounds according to the invention (depending on their respective structure and the application rate applied) have outstanding growth-regulatory properties in crop plants. They engage in the plant metabolism in a regulatory fashion and can therefore be employed for the influencing, in a targeted manner, of plant constituents and for facilitating harvesting, such as, for example, by triggering desiccation and stunted growth. Moreover, they are also suitable for generally controlling and inhibiting undesired vegetative growth without destroying the plants in the process. Inhibiting the vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops since for example lodging can be reduced, or prevented completely, hereby.

Owing to their herbicidal and plant-growth-regulatory properties, the active substances can also be employed for controlling harmful plants and crops of genetically modified plants or plants which have been modified by conventional mutagenesis. As a rule, the transgenic plants are distinguished by especially advantageous properties, for example by resistances to certain pesticides, mainly certain herbicides, resistances to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate for example to the harvested material with regard to quantity, quality, storability, composition and specific constituents. Thus, transgenic plants with an increased starch content or a modified starch quality or those with a different fatty acid composition of the harvested material are known.

As regards transgenic crops, the use of the compounds according to the invention in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, sorghum and millet, rice and maize or else crops of sugar beet, cotton, soybean, oil seed rape, potato, tomato, peas and other vegetables is preferred. It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

It is preferred to use the compounds according to the invention or their salts in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, sorghum and millet, rice, cassava and maize or else crops of sugar beet, cotton, soybean, oil seed rape, potato, tomato, peas and other vegetables. It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

Conventional ways of generating novel plants which, in comparison with existing plants, have modified properties are, for example, traditional breeding methods and the generation of mutants. Alternatively, novel plants with modified properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, the following have been described in several cases:

-   -   recombinant modifications of crop plants for the purposes of         modifying the starch synthetized in the plants (for example WO         92/11376, WO 92/14827, WO 91/19806),     -   transgenic crop plants which are resistant to certain herbicides         of the glufosinate type (cf., for example, EP-A-0242236,         EP-A-242246) or of the glyphosate type (WO 92/00377) or of the         sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),     -   transgenic crop plants, for example cotton, which is capable of         producing Bacillus thuringiensis toxins (Bt toxins), which make         the plants resistant to certain pests (EP-A-0142924,         EP-A-0193259),     -   transgenic crop plants with a modified fatty acid composition         (WO 91/13972),     -   genetically modified crop plants with novel constituents or         secondary metabolites, for example novel phytoalexins, which         bring about an increased disease resistance (EPA 309862,         EPA0464461),     -   genetically modified plants with reduced photorespiration which         feature higher yields and higher stress tolerance (EPA 0305398),     -   transgenic crop plants which produce pharmaceutically or         diagnostically important proteins (“molecular pharming”),     -   transgenic crop plants which are distinguished by higher yields         or better quality,     -   transgenic crop plants which are distinguished by a combination,         for example of the abovementioned novel properties (“gene         stacking”).

A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known in principle; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg. or Christou, “Trends in Plant Science” 1 (1996) 423-431).

To carry out such recombinant manipulations, it is possible to introduce nucleic acid molecules into plasmids, which permit a mutagenesis or sequence modification by recombination of DNA sequences. For example, base substitutions can be carried out, part-sequences can be removed, or natural or synthetic sequences may be added with the aid of standard methods. To link the DNA fragments with one another, it is possible to add adapters or linkers to the fragments; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2. ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene and Klone”, VCH Weinheim 2. ed., 1996

The generation of plant cells with a reduced activity for a gene product can be achieved for example by the expression of at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect or by the expression of at least one correspondingly constructed ribozym, which specifically cleaves transcripts of the abovementioned gene product. To do this, it is possible firstly to use DNA molecules which comprise all of the coding sequence of a gene product, including any flanking sequences which may be present, or else DNA molecules which only comprise parts of the coding sequence, it being necessary for these parts to be long enough to bring about an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology with the coding sequences of a gene product, but which are not entirely identical.

When expressing nucleic acid molecules in plants, the protein synthetized may be localized in any compartment of the plant cell. In order to achieve localization in a particular compartment, however, it is possible for example to link the coding region to DNA sequences which ensure the localization in a specific compartment. Such sequences are known to the skilled worker (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). However, the nucleic acid molecules can also be expressed in the organelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques to give intact plants. In principle, the transgenic plants may be plants of any plant species, that is to say both monocotyledonous and dicotyledonous plants.

Thus, transgenic plants can be obtained which feature modified properties as the result of overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.

It is preferred to employ the compounds according to the invention in transgenic crops which are resistant to growth regulators such as, for example, dicamba, or against herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or against herbicides from the group of the sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and analogous active substances.

When the active substances according to the invention are used in transgenic crops, effects are frequently observed—in addition to the effects on harmful plants which can be observed in other crops—which are specific for the application in the transgenic crop in question, for example a modified or specifically widened spectrum of weeds which can be controlled, modified application rates which may be employed for application, preferably good combiningability with the herbicides to which the transgenic crop is resistant, and an effect on growth and yield of the transgenic crop plants.

The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.

The compounds according to the invention can be employed in the customary preparations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules. The invention therefore also relates to herbicidal and plant-growth-regulating compositions which comprise the compounds according to the invention.

The compounds according to the invention can be formulated in various ways, depending on the prevailing biological and/or physico-chemical parameters. Examples of possible formulations are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), seed-dressing products, granules for application by broadcasting and on the soil, granules (GR) in the form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual types of formulation are known in principle and are described, for example, in: Winnacker-Küchler, “Chemische Technologie” [Chemical technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials, surfactants, solvents and further additives, are also known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H. v. Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie” [Chemical technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

Based on these formulations, it is also possible to prepare combinations with other pesticidally active substances such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and/or growth regulators, for example in the form of a ready mix or a tank mix.

Wettable powders are preparations which are uniformly dispersible in water and which, besides the active substance, also comprise ionic and/or nonionic surfactants (wetters, dispersers), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurinate, besides a diluent or inert substance. To prepare the wettable powders, the herbicidally active substances are ground finely, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and mixed with the formulation auxiliaries, either simultaneously or subsequently.

Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylarylpolyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan esters such as, for example, sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as, for example, polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active substance with finely divided solid materials such as, for example, talcum, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates can be water- or oil-based. They can be prepared for example by wet-grinding by means of commercially available bead mills, if appropriate with addition of surfactants as already listed above for example in the case of the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared for example by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if appropriate, surfactants, as have already been mentioned for example above for the other formulation types.

Granules can be prepared either by spraying the active substance onto adsorptive, granulated inert material, or by applying active substance concentrates to the surface of carriers such as sand, kaolinites or granulated inert material with the aid of stickers, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active substances can also be granulated in the manner which is customary for the production of fertilizer granules, if desired as a mixture with fertilizers.

Water-dispersible granules are generally prepared by customary methods such as spray drying, fluidized-bed granulation, disk granulation, mixing with high-speed stirrers, and extrusion without solid inert material.

To prepare disk granules, fluidized-bed granules, extruder granules and spray granules, see, for example, methods in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 et seq.; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, p. 8-57.

For further details of the formulation of crop protection products see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

As a rule, the agrochemical preparations comprise from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention. In wettable powders, the active substance concentration is, for example, approximately 10 to 90% by weight, the remainder to 100% by weight being composed of customary formulation constituents. In the case of emulsifiable concentrates, the active substance concentration can amount to approximately 1 to 90, preferably 5 to 80% by weight. Formulations in the form of dusts comprise from 1 to 30% by weight of active substance, preferably in most cases from 5 to 20% by weight of active substance, and sprayable solutions comprise approximately from 0.05 to 80, preferably from 2 to 50% by weight of active substance. In the case of water-dispersible granules, the active substance content depends partly on whether the active compound is in liquid or solid form, and on the granulation auxiliaries, fillers and the like which are being used. In the case of the water-dispersible granules, for example, the active substance content is between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the active substance formulations mentioned comprise, if appropriate, the auxiliaries which are conventional in each case, such as stickers, wetters, dispersants, emulsifiers, penetrations, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors, and pH and viscosity regulators.

Based on these formulations, it is also possible to prepare combinations with other pesticidally active substances such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and/or growth regulators, for example in the form of a ready mix or a tank mix.

Active substances which can be employed in combination with the compounds according to the invention in mixed formulations or in the tank mix are, for example, known active substances which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoen desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 and the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds according to the invention are, for example, the following active substances (the compounds are either designated by the common name according to the International Organization for Standardization (ISO) or by a chemical name, if appropriate together with the code number) and always comprise all use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers. In this context, one and in some cases also several use forms are mentioned by way of example:

acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryne, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate, ancymidol, anilofos, asulam, atrazine, azafenidin, azimsulfuron, aziprotryne, BAH-043, BAS-140H, BAS-693H, BAS-714H, BAS-762H, BAS-776H, BAS-800H, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclon, benzofenap, benzofluor, benzoylprop, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron, buminafos, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorazifop, chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat-chloride, chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlorotoluron, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D, 2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet, n-decanol, desmedipham, desmetryn, detosyl-pyrazolate (DTP), di-allate, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dikegulac-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethephon, ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5331, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoro-propyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]ethanesulfonamide, fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, fenuron, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen, foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellic acid, glufosinate, L-glufosinate, L-glufosinate-ammonium, glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, H-9201, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HNPC-9908, HOK-201, HW-02, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, inabenfide, indanofan, indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, isocarbamid, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KUH-043, KUH-071, karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mepiquat-chloride, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, methazole, methoxyphenone, methyldymron, 1-methylcyclopropene, methyl isothiocyanate, metobenzuron, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monocarbamide, monocarbamide dihydrogen sulfate, monolinuron, monosulfuron, monuron, MT 128, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide, NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrophenolat-sodium (isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paclobutrazole, paraquat, paraquat dichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazole, profluazol, procyazine, prodiamine, prifluraline, profoxydim, prohexadione, prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyzamide, prosulfalin, prosulfocarb, prosulfuron, prynachlor, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, secbumeton, sethoxydim, siduron, simazine, simetryn, SN-106279, sulcotrione, sulf-allate (CDEC), sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate (glyphosate-trimesium), sulfosulfuron, SYN-523, SYP-249, SYP-298, SYP-300, tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryne, TH-547, thenylchlor, thiafluamide, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, tri-allate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl, tritosulfuron, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0166, ZJ-0270, ZJ-0543, ZJ-0862 and the following compounds

For use, the formulations, which are present in commercially available form, if appropriate, are diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dusts, soil granules, granules for broadcasting, and sprayable solutions, are usually not diluted further with further inert substances prior to use.

The application rate required of the compounds of the formula (I) varies as a function of the external conditions such as temperature, humidity, the nature of the herbicide used and the like. It can vary within wide limits, for example between 0.001 and 1.0 kg/ha and more of active substance, but it is preferably between 0.005 and 750 g/ha.

The examples which follow are intended to illustrate the invention.

A. CHEMICAL EXAMPLES 1. Preparation of 5-cyclopropyl-4-(3-methylamino-2-methylsulfonyl-4-trifluoromethylbenzoyl)isoxazole (No. 184 of table A) Step 1: Synthesis of 3-fluoro-2-methylthio-4-trifluoromethylbenzoic Acid

25.0 g (120.1 mmol) of 3-fluoro-4-trifluoromethylbenzoic acid were dissolved in 250 ml of dry tetrahydrofuran (THF), and 100.9 ml of n-butyllithium (2.5 M in hexane, 252.3 mmol) were added dropwise at −40° C. The mixture was stirred for 3 h, and a solution of 32.5 ml (360.4 mmol) of dimethyl disulfide in 50 ml of dry THF was then added dropwise. The mixture was stirred for 16 h, during which process, after half an hour, the temperature climbed slowly to RT. For work-up, 2 M HCl was added carefully. The mixture was extracted with diethyl ether, and the organic phase was subsequently extracted with 2 M NaOH. The aqueous phase was acidified and extracted with diethyl ether. The organic phase was washed with water, dried, and the solvent was removed in vacuo. The residue was stirred with n-heptane and the solid was separated off by a filtration. This gave 17.0 g of crude product, which was employed in the next synthesis step without further purification.

Step 2: Synthesis of 3-fluoro-2-methylsulfonyl-4-trifluoromethylbenzoic Acid

18.6 g (73.2 mmol) of 3-fluoro-2-methylthio-4-trifluoromethylbenzoic acid were introduced into 180 ml of glacial acetic acid. 724 mg (2.2 mmol) of sodium tungstate(VI)dihydrate were added, and the mixture was then heated to 50-60° C. 15.0 ml (30% strength, 146.8 mmol) of an aqueous hydrogen peroxide solution were added dropwise at this temperature. The mixture was stirred for 4.5 h at this temperature. To complete the reaction, 14.9 ml (30% strength, 145.9 mmol) of an aqueous H₂O₂ solution were subsequently carefully added dropwise, and the contents stirred for another 3 h at 50-60° C. The reaction mixture was cooled and, for work-up, poured into water. The mixture was extracted twice using ethyl acetate, the combined organic phases were washed with an aqueous saturated sodium hydrogen sulfite solution, and, after the absence of peroxides has been determined analytically, the mixture was dried and the solvent was removed in vacuo. This gave 19.8 g of product in 95% purity.

Step 3: Synthesis of 3-methylamino-2-methylsulfonyl-4-trifluoromethylbenzoic Acid

2.40 g (8.4 mmol) of 3-fluoro-2-methylsulfonyl-4-trifluoromethylbenzoic acid were treated with 12.1 ml (168 mmol; 40 percent strength) of aqueous methylamine solution and the mixture was stirred for 4 h at RT. For work-up, the contents were poured into 6 N HCl, the mixture was subsequently cooled in an ice-bath. The precipitate was filtered off with suction. This gave 2.50 g of product in 95% purity.

Step 4: Synthesis of tert-butyl 3-cyclopropyl-2-(3-methylamino-2-methylsulfonyl-4-trifluoroethylbenzoyl)-3-oxopropanoate

2.50 g (8.4 mmol) of 3-methylamino-2-methylsulfonyl-4-trifluoromethylbenzoic acid were introduced into 50 ml of CH₂Cl₂ and treated with 1.1 ml (12.6 mmol) oxalyl dichloride and two drops of DMF. The mixture was heated at reflux until the evolution of gas had ceased. To complete the reaction, another 0.8 ml (9.2 mmol) of oxalyl dichloride and two more drops of DMF were added. After the evolution of gas had ceased, the contents were heated at reflux for another 15 min. Thereafter, the mixture was concentrated on a rotary evaporator. To remove a residual oxalyl dichloride, the residue was coevaporated with toluene. The residue was taken up in 50 ml of toluene. 4.01 g (16.8 mmol) of magnesium (3-tert.-butoxy-1-cyclopropyl-3-oxoprop-1-en-1-olate)methoxide (synthesis described for example in EP 0918056) were added, and the mixture was stirred for 16 h at RT. The contents were concentrated and the residue was taken up in ethyl acetate. The solution was washed with dilute HCl, the organic phase was dried, and the solvent was removed in vacuo. This gave 5.3 g of crude product in approximately 70% purity, which was employed in the next synthesis step without further purification.

Step 5: Synthesis of 1-cyclopropyl-3-(3-methylamino-2-methylsulfonyl-4-trifluoromethylphenyl)propane-1,3-dione

5.0 ml of trifluoroacetic acid were heated at 55°-60° C. A solution of 5.3 g (8.0 mmol; 70% purity) of tert-butyl-3-cyclopropyl-2-(3-methylamino-2-methylsulfonyl-4-trifluoromethylbenzoyl)-3-oxopropanoate in 10 ml of CH₂Cl₂ was added dropwise and the mixture was then heated at reflux for 15 min. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel. This gave 1.22 g of product in 95% purity.

Step 6: Synthesis of 1-cyclopropyl-2-(dimethylaminomethylidene)-3-(3-methylamino-2-methylsulfonyl-4-trifluoromethylphenyl)propane-1,3-dione

1.22 g (3.4 mmol) of 1-cyclopropyl-3-(3-methylamino-2-methylsulfonyl-4-trifluoromethylphenyl)propane-1,3-dione were treated with 3.0 ml (22.7 mmol) of N,N-dimethyl formamide dimethyl acetal and the mixture was stirred for 16 h at RT. Then, a little n-heptane was added, and the contents were stirred for a further 10 min at RT. The precipitate was filtered off with suction. This gave 1.29 g of product in 95% purity.

Step 7: Synthesis of 5-cyclopropyl-4-(3-methylamino-2-methylsulfonyl-4-trifluoromethylbenzoyl)isoxazole

1.29 g (3.1 mmol) of 1-cyclopropyl-2-(dimethylaminomethylidene)-3-(3-methylamino-2-methylsulfonyl-4-trifluoromethylphenyl)propane-1,3-dione were introduced into 50 ml of ethanol. 0.30 g (4.3 mmol) of hydroxylammonium chloride was added, and the mixture was stirred for 30 min at RT. Thereafter, 0.33 g (4.0 mmol) of sodium acetate was added, and the contents were stirred for 16 h at RT. Thereupon, a further 0.15 g (2.2 mmol) of hydroxylammonium chloride was added, and, again, the mixture was stirred for 16 h at RT. Thereafter, a further 0.15 g (2.2 mmol) of hydroxylammonium chloride was added, and the mixture was stirred for a further 3 d at RT. The solvent was removed in vacuo, and the residue was taken up in ethyl acetate. The solution was washed with 1 N HCl, the organic phase was dried, and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel. This gave 1.00 g of product in 95% purity.

2. Preparation of 5-cyclopropyl-4-(3-methylamino-2-methyl-4-methylsulfonyl-benzoyl)isoxazole (No. 2 of Table A) Step 1: Synthesis of 1-cyclopropyl-2-(dimethylaminomethylidene)-3-(3-methylamino-2-methyl-4-methylsulfonylphenyl)propane-1,3-dione

A solution of 1.58 g (5.1 mmol) of 1-cyclopropyl-3-(3-methylamino-2-methyl-4-methylsulfonylphenyl)propane-1,3-dione and 2.0 ml (15.3 mmol) of N,N-dimethyl formamide dimethyl acetal was stirred for 3 h at RT. The mixture was treated with 10 ml of CH₂Cl₂, stirred for 2 h at an oil-bath temperature of 50° C., left to stand overnight, stirred for 1 d at an oil-bath temperature of 50° C., and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel. This gave 0.85 g of product in 93% purity.

Step 2: Synthesis of 5-cyclopropyl-4-(3-methylamino-2-methyl-4-methylsulfonyl-benzoyl)isoxazole

0.19 g (2.8 mmol) of hydroxylammonium chloride was added to a solution of 0.85 g (2.3 mmol) of 1-cyclopropyl-2-(dimethylaminomethylidene)-3-(3-methylamino-2-methyl-4-methylsulfonylphenyl)propane-1,3-dione in 100 ml of ethanol. The mixture was stirred for 3 h at RT, and the solvent was removed in vacuo. The residue was taken up in CH₂Cl₂, washed with 10% strength H₂SO₄ and dried over MgSO₄. The solvent was removed in vacuo, and the residue was purified by column chromatography on silica gel. This gave 0.50 g of product in 95% purity.

The examples listed in the tables hereinbelow were prepared analogously to abovementioned methods or are obtainable analogously to abovementioned methods. These compounds are very particularly preferred.

The abbreviations used are:

All=allyl Et=ethyl Me=methyl Pr=propyl

TABLE A Compounds of the formula (I) according to the invention (I)

Physical data: No. X Y A Z ¹H NMR: δ [CDCl₃]  1 Me SO₂Me NH₂ H 8.18 (s, 1H), 7.76 (d, 1H), 6.80 (d, 1H), 5.32 (br, 2H), 3.11 (s, 3H), 2.62-2.71 (m, 1H), 2.18 (s, 3H), 1.34-1.40 (m, 2H), 1.22-1.29 (m, 2H)  2 Me SO₂Me NHMe H 8.21 (s, 1H), 7.82 (d,1H), 6.96 (d, 1H), 5.62 (br, 1H), 3.09 (s, 3H), 3.01 (s, 3H), 2.56-2.64 (m, 1H), 2.32 (s, 3H), 1.33- 1.40 (m, 2H), 1.21-1.27 (m, 2H)  3 Me SO₂Me NHEt H 8.21 (s, 1H), 7.82 (d, 1H), 6.97 (d, 1H), 5.55 (br, 1H), 3.27 (q, 2H), 3.11 (s, 3H), 2.57-2.65 (m, 1H), 2.29 (s, 3H), 1.33- 1.39 (m, 2H), 1.31 (t, 3H), 1.22-1.28 (m, 2H)  4 Me SO₂Me NH-n-Pr H 8.21 (s, 1H), 7.82 (d, 1H), 6.95 (d, 1H), 5.68 (br, 1H), 3.18 (dd, 2H), 3.11 (s, 3H), 2.56-2.63 (m, 1H), 2.29 (s, 3H), 1.66-1.76 (m, 2H), 1.34-1.39 (m, 2H), 1.21-1.28 (m, 2H), 1.03 (t, 3H)  5 Me SO₂Me NHAll H 8.19 (s, 1H), 7.84 (d, 1H), 6.98 (d, 1H), 5.93.6.05 (m, 1H), 5.68 (br, 1H), 5.32- 5.39 (m, 1H), 5.2-5.25 (m, 1H), 3.82- 3.88 (m, 2H), 3.11 (s, 3H), 2.58-2.66 (m, 1H), 2.29 (s, 3H), 1.33-1.39 (m, 2H), 1.21-1.28 (m, 2H)  6 Me SO₂Me NH(CH₂)₂O—Me H 8.21 (s, 1H), 7.84 (d, 1H), 6.97 (d, 1H), 5.81 (br, 1H), 3.62 (dd, 2H), 3.42 (br, 2H), 3.41 (s, 3H), 3.21 (s, 3H), 2.54-2.62 (m, 1H), 2.29 (s, 3H), 1.33-1.39 (m, 2H), 1.21-1.28 (m, 2H)  7 Me SO₂Me NH(CH₂)₂O—Et H 8.22 (s, 1H), 7.84 (d, 1H), 6.97 (d, 1H), 5.84 (br, 1H), 3.66 (dd, 2H), 3.57 (q, 2H), 3.42 (dd, 2H), 3.21 (s, 3H), 2.53- 2.63 (m, 1H), 2.29 (s, 3H), 1.32-1.40 (m, 2H), 1.24 (t, 3H), 1.19-1.29 (m, 2H)  8 Me SO₂Me NH(CH₂)₃O—Me H 8.21 (s, 1H), 7.83 (d,1H), 6.98 (d, 1H), 5.64 (br, 1H), 3.55 (t, 2H), 3.37 (s, 3H), 3.32 (t, 2H), 3.13 (s, 3H), 2.55-2.63 (m, 1H), 2.30 (s, 3H), 1.90-1.99 (m, 2H), 1.34-1.39 (m, 2H), 1.21-1.28 (m, 2H)  9 Me SO₂Me N═CH—NMe₂ H  10 Me SO₂Me NH₂ CO₂Me  11 Me SO₂Me NHMe CO₂Me  12 Me SO₂Me NHEt CO₂Me  13 Me SO₂Me NH-n-Pr CO₂Me  14 Me SO₂Me NHAll CO₂Me  15 Me SO₂Me NH(CH₂)₂O—Me CO₂Me  16 Me SO₂Me N═CH—NMe₂ CO₂Me  17 Me SO₂Me N═CH—NMe₂ CO₂Et  18 Me SO₂Me NH₂ CO₂Et  19 Me SO₂Me NHMe CO₂Et  20 Me SO₂Me NHEt CO₂Et  21 Me SO₂Me NH-n-Pr CO₂Et  22 Me SO₂Me NHAll CO₂Et  23 Me SO₂Me NH(CH₂)₂O—Me CO₂Et  24 Me SO₂Me NMe₂ H 8.18 (s, 1H), 8.04 (d, 1H), 7.32 (d, 1H), 3.29 (s, 3H), 2.93 (s, 6H), 2.58-2.66 (m, 1H), 2.37 (s, 3H), 1.34-1.40 (m, 2H), 1.22-1.29 (m, 2H)  25 Me SO₂Me N(Me)Et H  26 Me SO₂Me N(Me)-n-Pr H  27 Me SO₂Me N(Me)All H  28 Me SO₂Me N(Me)(CH₂)₂O—Me H  29 Me SO₂Me NMe₂ CO₂Me  30 Me SO₂Me N(Me)Et CO₂Me  31 Me SO₂Me N(Me)-n-Pr CO₂Me  32 Me SO₂Me N(Me)All CO₂Me  33 Me SO₂Me N(Me)(CH₂)₂O—Me CO₂Me  34 Me SO₂Me NMe₂ CO₂Et  35 Me SO₂Me N(Me)Et CO₂Et  36 Me SO₂Me N(Me)-n-Pr CO₂Et  37 Me SO₂Me N(Me)All CO₂Et  38 Me SO₂Me N(Me)(CH₂)₂O—Me CO₂Et  39 Me CF₃ NH₂ H  40 Me CF₃ NHMe H  41 Me CF₃ NHEt H  42 Me CF₃ NH-n-Pr H  43 Me CF₃ NHAll H  44 Me CF₃ NH(CH₂)₂O—Me H  45 Me CF₃ N═CH—NMe₂ H  46 Me CF₃ NH₂ CO₂Me  47 Me CF₃ NHMe CO₂Me  48 Me CF₃ NHEt CO₂Me  49 Me CF₃ NH-n-Pr CO₂Me  50 Me CF₃ NHAll CO₂Me  51 Me CF₃ NH(CH₂)₂O—Me CO₂Me  52 Me CF₃ N═CH—NMe₂ CO₂Me  53 Me CF₃ NH₂ CO₂Et  54 Me CF₃ NHMe CO₂Et  55 Me CF₃ NHEt CO₂Et  56 Me CF₃ NH-n-Pr CO₂Et  57 Me CF₃ NHAll CO₂Et  58 Me CF₃ NH(CH₂)₂O—Me CO₂Et  59 Me CF₃ N═CH—NMe₂ CO₂Et  60 Me CF₃ NMe₂ H  61 Me CF₃ N(Me)Et H  62 Me CF₃ N(Me)-n-Pr H  63 Me CF₃ N(Me)All H  64 Me CF₃ N(Me)(CH₂)₂O—Me H  65 Me CF₃ NMe₂ CO₂Me  66 Me CF₃ N(Me)Et CO₂Me  67 Me CF₃ N(Me)-n-Pr CO₂Me  68 Me CF₃ N(Me)All CO₂Me  69 Me CF₃ N(Me)(CH₂)₂O—Me CO₂Me  70 Me CF₃ NMe₂ CO₂Et  71 Me CF₃ N(Me)Et CO₂Et  72 Me CF₃ N(Me)-n-Pr CO₂Et  73 Me CF₃ N(Me)All CO₂Et  74 Me CF₃ N(Me)(CH₂)₂O—Me CO₂Et  75 Me Cl NH₂ H  76 Me Cl NHMe H  77 Me Cl NHEt H  78 Me Cl NH-n-Pr H  79 Me Cl NHAll H  80 Me Cl NH(CH₂)₂O—Me H  81 Me Cl N═CH—NMe₂ H  82 Me Cl NH₂ CO₂Me  83 Me Cl NHMe CO₂Me  84 Me Cl NHEt CO₂Me  85 Me Cl NH-n-Pr CO₂Me  86 Me Cl NHAll CO₂Me  87 Me Cl NH(CH₂)₂O—Me CO₂Me  88 Me Cl N═CH—NMe₂ CO₂Me  89 Me Cl NH₂ CO₂Et  90 Me Cl NHMe CO₂Et  91 Me Cl NHEt CO₂Et  92 Me Cl NH-n-Pr CO₂Et  93 Me Cl NHAll CO₂Et  94 Me Cl NH(CH₂)₂O—Me CO₂Et  95 Me Cl N═CH—NMe₂ CO₂Et  96 Me Cl NMe₂ H  97 Me Cl N(Me)Et H  98 Me Cl N(Me)-n-Pr H  99 Me Cl N(Me)All H 100 Me Cl N(Me)(CH₂)₂O—Me H 101 Me Cl NMe₂ CO₂Me 102 Me Cl N(Me)Et CO₂Me 103 Me Cl N(Me)-n-Pr CO₂Me 104 Me Cl N(Me)All CO₂Me 105 Me Cl N(Me)(CH₂)₂O—Me CO₂Me 106 Me Cl NMe₂ CO₂Et 107 Me Cl N(Me)Et CO₂Et 108 Me Cl N(Me)-n-Pr CO₂Et 109 Me Cl N(Me)All CO₂Et 110 Me Cl N(Me)(CH₂)₂O—Me CO₂Et 111 Me OMe NH₂ H 112 Me OMe NHMe H 113 Me OMe NHEt H 114 Me OMe NH-n-Pr H 115 Me OMe NHAll H 116 Me OMe NH(CH₂)₂O—Me H 117 Me OMe N═CH—NMe₂ H 118 Me OMe NH₂ CO₂Me 119 Me OMe NHMe CO₂Me 120 Me OMe NHEt CO₂Me 121 Me OMe NH-n-Pr CO₂Me 122 Me OMe NHAll CO₂Me 123 Me OMe NH(CH₂)₂O—Me CO₂Me 124 Me OMe N═CH—NMe₂ CO₂Me 125 Me OMe NH₂ CO₂Et 126 Me OMe NHMe CO₂Et 127 Me OMe NHEt CO₂Et 128 Me OMe NH-n-Pr CO₂Et 129 Me OMe NHAll CO₂Et 130 Me OMe NH(CH₂)₂O—Me CO₂Et 131 Me OMe N═CH—NMe₂ CO₂Et 132 Me OMe NMe₂ H 133 Me OMe N(Me)Et H 134 Me OMe N(Me)-n-Pr H 135 Me OMe N(Me)All H 136 Me OMe N(Me)(CH₂)₂O—Me H 137 Me OMe NMe₂ CO₂Me 138 Me OMe N(Me)Et CO₂Me 139 Me OMe N(Me)-n-Pr CO₂Me 140 Me OMe N(Me)All CO₂Me 141 Me OMe N(Me)(CH₂)₂O—Me CO₂Me 142 Me OMe NMe₂ CO₂Et 143 Me OMe N(Me)Et CO₂Et 144 Me OMe N(Me)-n-Pr CO₂Et 145 Me OMe N(Me)All CO₂Et 146 Me OMe N(Me)(CH₂)₂O—Me CO₂Et 147 SO₂Me SO₂Me NH₂ H 148 SO₂Me SO₂Me NHMe H 149 SO₂Me SO₂Me NHEt H 150 SO₂Me SO₂Me NH-n-Pr H 151 SO₂Me SO₂Me NHAll H 152 SO₂Me SO₂Me NH(CH₂)₂O—Me H 153 SO₂Me SO₂Me N═CH—NMe₂ H 154 SO₂Me SO₂Me NH₂ CO₂Me 155 SO₂Me SO₂Me NHMe CO₂Me 156 SO₂Me SO₂Me NHEt CO₂Me 157 SO₂Me SO₂Me NH-n-Pr CO₂Me 158 SO₂Me SO₂Me NHAll CO₂Me 159 SO₂Me SO₂Me NH(CH₂)₂O—Me CO₂Me 160 SO₂Me SO₂Me N═CH—NMe₂ CO₂Me 161 SO₂Me SO₂Me NH₂ CO₂Et 162 SO₂Me SO₂Me NHMe CO₂Et 163 SO₂Me SO₂Me NHEt CO₂Et 164 SO₂Me SO₂Me NH-n-Pr CO₂Et 165 SO₂Me SO₂Me NHAll CO₂Et 166 SO₂Me SO₂Me NH(CH₂)₂O—Me CO₂Et 167 SO₂Me SO₂Me N═CH—NMe₂ CO₂Et 168 SO₂Me SO₂Me NMe₂ H 169 SO₂Me SO₂Me N(Me)Et H 170 SO₂Me SO₂Me N(Me)-n-Pr H 171 SO₂Me SO₂Me N(Me)All H 172 SO₂Me SO₂Me N(Me)(CH₂)₂O—Me H 173 SO₂Me SO₂Me NMe₂ CO₂Me 174 SO₂Me SO₂Me N(Me)Et CO₂Me 175 SO₂Me SO₂Me N(Me)-n-Pr CO₂Me 176 SO₂Me SO₂Me N(Me)All CO₂Me 177 SO₂Me SO₂Me N(Me)(CH₂)₂O—Me CO₂Me 178 SO₂Me SO₂Me NMe₂ CO₂Et 179 SO₂Me SO₂Me N(Me)Et CO₂Et 180 SO₂Me SO₂Me N(Me)-n-Pr CO₂Et 181 SO₂Me SO₂Me N(Me)All CO₂Et 182 SO₂Me SO₂Me N(Me)(CH₂)₂O—Me CO₂Et 183 SO₂Me CF₃ NH₂ 8.21 (s, 1H), 7.72 (d,1H), 6.67 (d, 1H), 6.12 (br. s, 2H), 3.25 (s, 3H), 2.57 (m, 1H), 1.38-1.32 (m, 2H), 1.25-1.22 (m, 2H) 184 SO₂Me CF₃ NHMe H 8.19 (s, 1H), 7.83 (d, 1H), 6.97 (q, 1H), 6.68 (d, 1H), 3.23 (s, 3H), 3.12 (m, 3H), 2.57 (m, 1H), 1.37-1.32 (m, 2H), 1.26- 1.20 (m, 2H) 185 SO₂Me CF₃ NHEt H 8.21 (s, 1H), 7.83 (d,1H), 6.71 (d,1H), 6.63 (t, 1H), 3.42 (m, 2H), 3.27 (s, 3H), 2.58 (m, 1H), 1.38-1.32 (m, 2H), 1.25- 1.20 (m, 2H) 186 SO₂Me CF₃ NH-n-Pr H 187 SO₂Me CF₃ NHAll H 188 SO₂Me CF₃ NH(CH₂)₂O—Me H 189 SO₂Me CF₃ N═CH—NMe₂ H 190 SO₂Me CF₃ NH₂ CO₂Me 191 SO₂Me CF₃ NHMe CO₂Me 192 SO₂Me CF₃ NHEt CO₂Me 193 SO₂Me CF₃ NH-n-Pr CO₂Me 194 SO₂Me CF₃ NHAll CO₂Me 195 SO₂Me CF₃ NH(CH₂)₂O—Me CO₂Me 196 SO₂Me CF₃ N═CH—NMe₂ CO₂Me 197 SO₂Me CF₃ NH₂ CO₂Et 7.68 (d, 1H), 6.66 (d, 1H), 6.08 (br. s, 2H), 4.18 (q, 2H), 3.27 (s, 3H), 2.48 (m, 1H), 1.37-1.32 (m, 2H), 1.28-1.20 (t + m, 5H) 198 SO₂Me CF₃ NHMe CO₂Et 199 SO₂Me CF₃ NHEt CO₂Et 200 SO₂Me CF₃ NH-n-Pr CO₂Et 201 SO₂Me CF₃ NHAll CO₂Et 202 SO₂Me CF₃ NH(CH₂)₂O—Me CO₂Et 203 SO₂Me CF₃ N═CH—NMe₂ CO₂Et 204 SO₂Me CF₃ NMe₂ H 8.12 (s, 1H), 7.98 (d, 1H), 7.32 (d, 1H), 3.32 (s, 3H), 2.92 (s, 6H), 2.67 (m, 1H), 1.38-1.33 (m, 2H), 1.27-1.22 (m, 2H) 205 SO₂Me CF₃ N(Me)Et H 206 SO₂Me CF₃ N(Me)-n-Pr H 207 SO₂Me CF₃ N(Me)All H 208 SO₂Me CF₃ N(Me)(CH₂)₂O—Me H 209 SO₂Me CF₃ NMe₂ CO₂Me 210 SO₂Me CF₃ N(Me)Et CO₂Me 211 SO₂Me CF₃ N(Me)-n-Pr CO₂Me 212 SO₂Me CF₃ N(Me)All CO₂Me 213 SO₂Me CF₃ N(Me)(CH₂)₂O—Me CO₂Me 214 SO₂Me CF₃ NMe₂ CO₂Et 215 SO₂Me CF₃ N(Me)Et CO₂Et 216 SO₂Me CF₃ N(Me)-n-Pr CO₂Et 217 SO₂Me CF₃ N(Me)All CO₂Et 218 SO₂Me CF₃ N(Me)(CH₂)₂O—Me CO₂Et 219 SO₂Me Cl NH₂ H 220 SO₂Me Cl NHMe H 221 SO₂Me Cl NHEt H 222 SO₂Me Cl NH-n-Pr H 223 SO₂Me Cl NHAll H 224 SO₂Me Cl NH(CH₂)₂O—Me H 225 SO₂Me Cl N═CH—NMe₂ H 226 SO₂Me Cl NH₂ CO₂Me 227 SO₂Me Cl NHMe CO₂Me 228 SO₂Me Cl NHEt CO₂Me 229 SO₂Me Cl NH-n-Pr CO₂Me 230 SO₂Me Cl NHAll CO₂Me 231 SO₂Me Cl NH(CH₂)₂O—Me CO₂Me 232 SO₂Me Cl N═CH—NMe₂ CO₂Me 233 SO₂Me Cl NH₂ CO₂Et 234 SO₂Me Cl NHMe CO₂Et 235 SO₂Me Cl NHEt CO₂Et 236 SO₂Me Cl NH-n-Pr CO₂Et 237 SO₂Me Cl NHAll CO₂Et 238 SO₂Me Cl NH(CH₂)₂O—Me CO₂Et 239 SO₂Me Cl N═CH—NMe₂ CO₂Et 240 SO₂Me Cl NMe₂ H 241 SO₂Me Cl N(Me)Et H 242 SO₂Me Cl N(Me)-n-Pr H 243 SO₂Me Cl N(Me)All H 244 SO₂Me Cl N(Me)(CH₂)₂O—Me H 245 SO₂Me Cl NMe₂ CO₂Me 246 SO₂Me Cl N(Me)Et CO₂Me 247 SO₂Me Cl N(Me)-n-Pr CO₂Me 248 SO₂Me Cl N(Me)All CO₂Me 249 SO₂Me Cl N(Me)(CH₂)₂O—Me CO₂Me 250 SO₂Me Cl NMe₂ CO₂Et 251 SO₂Me Cl N(Me)Et CO₂Et 252 SO₂Me Cl N(Me)-n-Pr CO₂Et 253 SO₂Me Cl N(Me)All CO₂Et 254 SO₂Me Cl N(Me)(CH₂)₂O—Me CO₂Et 255 SO₂Me OMe NH₂ H 256 SO₂Me OMe NHMe H 257 SO₂Me OMe NHEt H 258 SO₂Me OMe NH-n-Pr H 259 SO₂Me OMe NHAll H 260 SO₂Me OMe NH(CH₂)₂O—Me H 261 SO₂Me OMe N═CH—NMe₂ H 262 SO₂Me OMe NH₂ CO₂Me 263 SO₂Me OMe NHMe CO₂Me 264 SO₂Me OMe NHEt CO₂Me 265 SO₂Me OMe NH-n-Pr CO₂Me 266 SO₂Me OMe NHAll CO₂Me 267 SO₂Me OMe NH(CH₂)₂O—Me CO₂Me 268 SO₂Me OMe N═CH—NMe₂ CO₂Me 269 SO₂Me OMe NH₂ CO₂Et 270 SO₂Me OMe NHMe CO₂Et 271 SO₂Me OMe NHEt CO₂Et 272 SO₂Me OMe NH-n-Pr CO₂Et 273 SO₂Me OMe NHAll CO₂Et 274 SO₂Me OMe NH(CH₂)₂O—Me CO₂Et 275 SO₂Me OMe N═CH—NMe₂ CO₂Et 276 SO₂Me OMe NMe₂ H 277 SO₂Me OMe N(Me)Et H 278 SO₂Me OMe N(Me)-n-Pr H 279 SO₂Me OMe N(Me)All H 280 SO₂Me OMe N(Me)(CH₂)₂O—Me H 281 SO₂Me OMe NMe₂ CO₂Me 282 SO₂Me OMe N(Me)Et CO₂Me 283 SO₂Me OMe N(Me)-n-Pr CO₂Me 284 SO₂Me OMe N(Me)All CO₂Me 285 SO₂Me OMe N(Me)(CH₂)₂O—Me CO₂Me 286 SO₂Me OMe NMe₂ CO₂Et 287 SO₂Me OMe N(Me)Et CO₂Et 288 SO₂Me OMe N(Me)-n-Pr CO₂Et 289 SO₂Me OMe N(Me)All CO₂Et 290 SO₂Me OMe N(Me)(CH₂)₂O—Me CO₂Et 291 CF₃ SO₂Me NH₂ H 292 CF₃ SO₂Me NHMe H 293 CF₃ SO₂Me NHEt H 294 CF₃ SO₂Me NH-n-Pr H 295 CF₃ SO₂Me NHAll H 296 CF₃ SO₂Me NH(CH₂)₂O—Me H 297 CF₃ SO₂Me N═CH—NMe₂ H 298 CF₃ SO₂Me NH₂ CO₂Me 299 CF₃ SO₂Me NHMe CO₂Me 300 CF₃ SO₂Me NHEt CO₂Me 301 CF₃ SO₂Me NH-n-Pr CO₂Me 302 CF₃ SO₂Me NHAll CO₂Me 303 CF₃ SO₂Me NH(CH₂)₂O—Me CO₂Me 304 CF₃ SO₂Me N═CH—NMe₂ CO₂Me 305 CF₃ SO₂Me NH₂ CO₂Et 306 CF₃ SO₂Me NHMe CO₂Et 307 CF₃ SO₂Me NHEt CO₂Et 308 CF₃ SO₂Me NH-n-Pr CO₂Et 309 CF₃ SO₂Me NHAll CO₂Et 310 CF₃ SO₂Me NH(CH₂)₂O—Me CO₂Et 311 CF₃ SO₂Me N═CH—NMe₂ CO₂Et 312 CF₃ SO₂Me NMe₂ H 313 CF₃ SO₂Me N(Me)Et H 314 CF₃ SO₂Me N(Me)-n-Pr H 315 CF₃ SO₂Me N(Me)All H 316 CF₃ SO₂Me N(Me)(CH₂)₂O—Me H 317 CF₃ SO₂Me NMe₂ CO₂Me 318 CF₃ SO₂Me N(Me)Et CO₂Me 319 CF₃ SO₂Me N(Me)-n-Pr CO₂Me 320 CF₃ SO₂Me N(Me)All CO₂Me 321 CF₃ SO₂Me N(Me)(CH₂)₂O—Me CO₂Me 322 CF₃ SO₂Me NMe₂ CO₂Et 323 CF₃ SO₂Me N(Me)Et CO₂Et 324 CF₃ SO₂Me N(Me)-n-Pr CO₂Et 325 CF₃ SO₂Me N(Me)All CO₂Et 326 CF₃ SO₂Me N(Me)(CH₂)₂O—Me CO₂Et 327 CF₃ Cl NH₂ H 328 CF₃ Cl NHMe H 329 CF₃ Cl NHEt H 330 CF₃ Cl NH-n-Pr H 331 CF₃ Cl NHAll H 332 CF₃ Cl NH(CH₂)₂O—Me H 333 CF₃ Cl N═CH—NMe₂ H 334 CF₃ Cl NH₂ CO₂Me 335 CF₃ Cl NHMe CO₂Me 336 CF₃ Cl NHEt CO₂Me 337 CF₃ Cl NH-n-Pr CO₂Me 338 CF₃ Cl NHAll CO₂Me 339 CF₃ Cl NH(CH₂)₂O—Me CO₂Me 340 CF₃ Cl N═CH—NMe₂ CO₂Me 341 CF₃ Cl NH₂ CO₂Et 342 CF₃ Cl NHMe CO₂Et 343 CF₃ Cl NHEt CO₂Et 344 CF₃ Cl NH-n-Pr CO₂Et 345 CF₃ Cl NHAll CO₂Et 346 CF₃ Cl NH(CH₂)₂O—Me CO₂Et 347 CF₃ Cl N═CH—NMe₂ CO₂Et 348 CF₃ Cl NMe₂ H 349 CF₃ Cl N(Me)Et H 350 CF₃ Cl N(Me)-n-Pr H 351 CF₃ Cl N(Me)All H 352 CF₃ Cl N(Me)(CH₂)₂O—Me H 353 CF₃ Cl NMe₂ CO₂Me 354 CF₃ Cl N(Me)Et CO₂Me 355 CF₃ Cl N(Me)-n-Pr CO₂Me 356 CF₃ Cl N(Me)All CO₂Me 357 CF₃ Cl N(Me)(CH₂)₂O—Me CO₂Me 358 CF₃ Cl NMe₂ CO₂Et 359 CF₃ Cl N(Me)Et CO₂Et 360 CF₃ Cl N(Me)-n-Pr CO₂Et 361 CF₃ Cl N(Me)All CO₂Et 362 CF₃ Cl N(Me)(CH₂)₂O—Me CO₂Et 363 CF₃ OMe NH₂ H 364 CF₃ OMe NHMe H 365 CF₃ OMe NHEt H 366 CF₃ OMe NH-n-Pr H 367 CF₃ OMe NHAll H 368 CF₃ OMe NH(CH₂)₂O—Me H 369 CF₃ OMe N═CH—NMe₂ H 370 CF₃ OMe NH₂ CO₂Me 371 CF₃ OMe NHMe CO₂Me 372 CF₃ OMe NHEt CO₂Me 373 CF₃ OMe NH-n-Pr CO₂Me 374 CF₃ OMe NHAll CO₂Me 375 CF₃ OMe NH(CH₂)₂O—Me CO₂Me 376 CF₃ OMe N═CH—NMe₂ CO₂Me 377 CF₃ OMe NH₂ CO₂Et 378 CF₃ OMe NHMe CO₂Et 379 CF₃ OMe NHEt CO₂Et 380 CF₃ OMe NH-n-Pr CO₂Et 381 CF₃ OMe NHAll CO₂Et 382 CF₃ OMe NH(CH₂)₂O—Me CO₂Et 383 CF₃ OMe N═CH—NMe₂ CO₂Et 384 CF₃ OMe NMe₂ H 385 CF₃ OMe N(Me)Et H 386 CF₃ OMe N(Me)-n-Pr H 387 CF₃ OMe N(Me)All H 388 CF₃ OMe N(Me)(CH₂)₂O—Me H 389 CF₃ OMe NMe₂ CO₂Me 390 CF₃ OMe N(Me)Et CO₂Me 391 CF₃ OMe N(Me)-n-Pr CO₂Me 392 CF₃ OMe N(Me)All CO₂Me 393 CF₃ OMe N(Me)(CH₂)₂O—Me CO₂Me 394 CF₃ OMe NMe₂ CO₂Et 395 CF₃ OMe N(Me)Et CO₂Et 396 CF₃ OMe N(Me)-n-Pr CO₂Et 397 CF₃ OMe N(Me)All CO₂Et 398 CF₃ OMe N(Me)(CH₂)₂O—Me CO₂Et 399 Cl SO₂Me NH₂ H 8.18 (s, 1H), 7.81 (d, 1H), 6.83 (d, 1H), 5.77 (br, 2H), 3.12 (s, 3H), 2.66-2.75 (m, 1H), 1.36-1.41 (m, 2H), 1.24-1.31 (m, 2H) 400 Cl SO₂Me NHMe H 401 Cl SO₂Me NHEt H 402 Cl SO₂Me NH-n-Pr H 8.18 (s, 1H), 7.89 (d,1H), 6.93 (d, 1H), 3.51 (t, 2H), 3.14 (s, 3H), 2.61-2.72 (m, 1H), 1.64-1.78 (m, 2H), 1.34-1.42 (m, 2H), 1.22-1.33 (m, 2H), 1.03 (t, 3H) 403 Cl SO₂Me NHAll H 404 Cl SO₂Me NH(CH₂)₂O—Me H 405 Cl SO₂Me N═CH—NMe₂ H 8.16 (s, 1H), 8.03 (d, 1H), 7.45 (s, 1H), 7.09 (d, 1H), 3.32 (s,3H), 3.13 (s, 3H), 3.09 (s, 3H), 2.69-2.82 (m, 1H), 1.35- 1.44 (m, 2H), 1.23-1.34 (m, 2H) 406 Cl SO₂Me NH₂ CO₂Me 407 Cl SO₂Me NHMe CO₂Me 408 Cl SO₂Me NHEt CO₂Me 409 Cl SO₂Me NH-n-Pr CO₂Me 410 Cl SO₂Me NHAll CO₂Me 411 Cl SO₂Me NH(CH₂)₂O—Me CO₂Me 412 Cl SO₂Me N═CH—NMe₂ CO₂Me 413 Cl SO₂Me NH₂ CO₂Et 414 Cl SO₂Me NHMe CO₂Et 415 Cl SO₂Me NHEt CO₂Et 416 Cl SO₂Me NH-n-Pr CO₂Et 417 Cl SO₂Me NHAll CO₂Et 418 Cl SO₂Me NH(CH₂)₂O—Me CO₂Et 419 Cl SO₂Me N═CH—NMe₂ CO₂Et 420 Cl SO₂Me NMe₂ H 421 Cl SO₂Me N(Me)Et H 422 Cl SO₂Me N(Me)-n-Pr H 423 Cl SO₂Me N(Me)All H 424 Cl SO₂Me N(Me)(CH₂)₂O—Me H 425 Cl SO₂Me NMe₂ CO₂Me 426 Cl SO₂Me N(Me)Et CO₂Me 427 Cl SO₂Me N(Me)-n-Pr CO₂Me 428 Cl SO₂Me N(Me)All CO₂Me 429 Cl SO₂Me N(Me)(CH₂)₂O—Me CO₂Me 430 Cl SO₂Me NMe₂ CO₂Et 431 Cl SO₂Me N(Me)Et CO₂Et 432 Cl SO₂Me N(Me)-n-Pr CO₂Et 433 Cl SO₂Me N(Me)All CO₂Et 434 Cl SO₂Me N(Me)(CH₂)₂O—Me CO₂Et 435 Cl CF₃ NH₂ H 436 Cl CF₃ NHMe H 437 Cl CF₃ NHEt H 438 Cl CF₃ NH-n-Pr H 439 Cl CF₃ NHAll H 440 Cl CF₃ NH(CH₂)₂O—Me H 441 Cl CF₃ N═CH—NMe₂ H 442 Cl CF₃ NH₂ CO₂Me 443 Cl CF₃ NHMe CO₂Me 444 Cl CF₃ NHEt CO₂Me 445 Cl CF₃ NH-n-Pr CO₂Me 446 Cl CF₃ NHAll CO₂Me 447 Cl CF₃ NH(CH₂)₂O—Me CO₂Me 448 Cl CF₃ N═CH—NMe₂ CO₂Me 449 Cl CF₃ NH₂ CO₂Et 450 Cl CF₃ NHMe CO₂Et 451 Cl CF₃ NHEt CO₂Et 452 Cl CF₃ NH-n-Pr CO₂Et 453 Cl CF₃ NHAll CO₂Et 454 Cl CF₃ NH(CH₂)₂O—Me CO₂Et 455 Cl CF₃ N═CH—NMe₂ CO₂Et 456 Cl CF₃ NMe₂ H 457 Cl CF₃ N(Me)Et H 458 Cl CF₃ N(Me)-n-Pr H 459 Cl CF₃ N(Me)All H 460 Cl CF₃ N(Me)(CH₂)₂O—Me H 461 Cl CF₃ NMe₂ CO₂Me 462 Cl CF₃ N(Me)Et CO₂Me 463 Cl CF₃ N(Me)-n-Pr CO₂Me 464 Cl CF₃ N(Me)All CO₂Me 465 Cl CF₃ N(Me)(CH₂)₂O—Me CO₂Me 466 Cl CF₃ NMe₂ CO₂Et 467 Cl CF₃ N(Me)Et CO₂Et 468 Cl CF₃ N(Me)-n-Pr CO₂Et 469 Cl CF₃ N(Me)All CO₂Et 470 Cl CF₃ N(Me)(CH₂)₂O—Me CO₂Et 471 Cl Cl NH₂ H 472 Cl Cl NHMe H 473 Cl Cl NHEt H 474 Cl Cl NH-n-Pr H 475 Cl Cl NHAll H 476 Cl Cl NH(CH₂)₂O—Me H 477 Cl Cl N═CH—NMe₂ H 478 Cl Cl NH₂ CO₂Me 479 Cl Cl NHMe CO₂Me 480 Cl Cl NHEt CO₂Me 481 Cl Cl NH-n-Pr CO₂Me 482 Cl Cl NHAll CO₂Me 483 Cl Cl NH(CH₂)₂O—Me CO₂Me 484 Cl Cl N═CH—NMe₂ CO₂Me 485 Cl Cl NH₂ CO₂Et 486 Cl Cl NHMe CO₂Et 487 Cl Cl NHEt CO₂Et 488 Cl Cl NH-n-Pr CO₂Et 489 Cl Cl NHAll CO₂Et 490 Cl Cl NH(CH₂)₂O—Me CO₂Et 491 Cl Cl N═CH—NMe₂ CO₂Et 492 Cl Cl NMe₂ H 493 Cl Cl N(Me)Et H 494 Cl Cl N(Me)-n-Pr H 495 Cl Cl N(Me)All H 496 Cl Cl N(Me)(CH₂)₂O—Me H 497 Cl Cl NMe₂ CO₂Me 498 Cl Cl N(Me)Et CO₂Me 499 Cl Cl N(Me)-n-Pr CO₂Me 500 Cl Cl N(Me)All CO₂Me 501 Cl Cl N(Me)(CH₂)₂O—Me CO₂Me 502 Cl Cl NMe₂ CO₂Et 503 Cl Cl N(Me)Et CO₂Et 504 Cl Cl N(Me)-n-Pr CO₂Et 505 Cl Cl N(Me)All CO₂Et 506 Cl Cl N(Me)(CH₂)₂O—Me CO₂Et 507 Cl OMe NH₂ H 508 Cl OMe NHMe H 509 Cl OMe NHEt H 510 Cl OMe NH-n-Pr H 511 Cl OMe NHAll H 512 Cl OMe NH(CH₂)₂O—Me H 513 Cl OMe N═CH—NMe₂ H 514 Cl OMe NH₂ CO₂Me 515 Cl OMe NHMe CO₂Me 516 Cl OMe NHEt CO₂Me 517 Cl OMe NH-n-Pr CO₂Me 518 Cl OMe NHAll CO₂Me 519 Cl OMe NH(CH₂)₂O—Me CO₂Me 520 Cl OMe N═CH—NMe₂ CO₂Me 521 Cl OMe NH₂ CO₂Et 522 Cl OMe NHMe CO₂Et 523 Cl OMe NHEt CO₂Et 524 Cl OMe NH-n-Pr CO₂Et 525 Cl OMe NHAll CO₂Et 526 Cl OMe NH(CH₂)₂O—Me CO₂Et 527 Cl OMe N═CH—NMe₂ CO₂Et 528 Cl OMe NMe₂ H 529 Cl OMe N(Me)Et H 530 Cl OMe N(Me)-n-Pr H 531 Cl OMe N(Me)All H 532 Cl OMe N(Me)(CH₂)₂O—Me H 533 Cl OMe NMe₂ CO₂Me 534 Cl OMe N(Me)Et CO₂Me 535 Cl OMe N(Me)-n-Pr CO₂Me 536 Cl OMe N(Me)All CO₂Me 537 Cl OMe N(Me)(CH₂)₂O—Me CO₂Me 538 Cl OMe NMe₂ CO₂Et 539 Cl OMe N(Me)Et CO₂Et 540 Cl OMe N(Me)-n-Pr CO₂Et 541 Cl OMe N(Me)All CO₂Et 542 Cl OMe N(Me)(CH₂)₂O—Me CO₂Et 543 OMe SO₂Me NH₂ H 8.24 (s, 1H), 7.60 (d, 1H), 6.80 (d, 1H), 5.48 (br, 2H), 3.78 (s, 3H), 3.12 (s, 3H), 2.75-2.85 (m, 1H), 1.35-1.40 (m, 2H), 1.22-1.35 (m, 2H) 544 OMe SO₂Me NHMe H 8.25 (s, 1H), 7.66 (d, 1H), 6.80 (d, 1H), 5.95 (br, 1H), 3.68 (s, 3H), 3.15 (d, 3H), 3.08 (s, 3H), 2.78-2.85 (m, 1H), 1.35- 1.40 (m, 2H), 1.25-1.30 (m, 2H) 545 OMe SO₂Me NHEt H 546 OMe SO₂Me NH-n-Pr H 547 OMe SO₂Me NHAll H 548 OMe SO₂Me NH(CH₂)₂O—Me H 549 OMe SO₂Me N═CH—NMe₂ H 7.80 (s, 1H), 7.65 (s, 1H), 7.35 (d, 1H), 6.40 (s, 1H), 3.65 (s, 3H), 3.35 (s, 3H), 3.08 (s, 3H), 3.05 (s, 3H), 1.75-1.85 (s, 1H), 1.20-1.25 (m, 2H), 0.98-1.05 (m, 2H) 550 OMe SO₂Me NH₂ CO₂Me 551 OMe SO₂Me NHMe CO₂Me 552 OMe SO₂Me NHEt CO₂Me 553 OMe SO₂Me NH-n-Pr CO₂Me 554 OMe SO₂Me NHAll CO₂Me 555 OMe SO₂Me NH(CH₂)₂O—Me CO₂Me 556 OMe SO₂Me N═CH—NMe₂ CO₂Me 557 OMe SO₂Me NH₂ CO₂Et 558 OMe SO₂Me NHMe CO₂Et 559 OMe SO₂Me NHEt CO₂Et 560 OMe SO₂Me NH-n-Pr CO₂Et 561 OMe SO₂Me NHAll CO₂Et 562 OMe SO₂Me NH(CH₂)₂O—Me CO₂Et 563 OMe SO₂Me N═CH—NMe₂ CO₂Et 564 OMe SO₂Me NMe₂ H 8.20 (s, 1H), 7.90 (d, 1H), 7.40 (d, 1H), 3.78 (s, 3H), 3.35 (d,3H), 3.90 (s, 6H), 2.78-2.85 (m, 1H), 1.38-1.42 (m, 2H), 1.25-1.32 (m, 2H) 565 OMe SO₂Me N(Me)Et H 566 OMe SO₂Me N(Me)-n-Pr H 567 OMe SO₂Me N(Me)All H 568 OMe SO₂Me N(Me)(CH₂)₂O—Me H 569 OMe SO₂Me NMe₂ CO₂Me 570 OMe SO₂Me N(Me)Et CO₂Me 571 OMe SO₂Me N(Me)-n-Pr CO₂Me 572 OMe SO₂Me N(Me)All CO₂Me 573 OMe SO₂Me N(Me)(CH₂)₂O—Me CO₂Me 574 OMe SO₂Me NMe₂ CO₂Et 575 OMe SO₂Me N(Me)Et CO₂Et 576 OMe SO₂Me N(Me)-n-Pr CO₂Et 577 OMe SO₂Me N(Me)All CO₂Et 578 OMe SO₂Me N(Me)(CH₂)₂O—Me CO₂Et 579 OMe CF₃ NH₂ H 580 OMe CF₃ NHMe H 581 OMe CF₃ NHEt H 582 OMe CF₃ NH-n-Pr H 583 OMe CF₃ NHAll H 584 OMe CF₃ NH(CH₂)₂O—Me H 585 OMe CF₃ N═CH—NMe₂ H 586 OMe CF₃ NH₂ CO₂Me 587 OMe CF₃ NHMe CO₂Me 588 OMe CF₃ NHEt CO₂Me 589 OMe CF₃ NH-n-Pr CO₂Me 590 OMe CF₃ NHAll CO₂Me 591 OMe CF₃ NH(CH₂)₂O—Me CO₂Me 592 OMe CF₃ N═CH—NMe₂ CO₂Me 593 OMe CF₃ NH₂ CO₂Et 594 OMe CF₃ NHMe CO₂Et 595 OMe CF₃ NHEt CO₂Et 596 OMe CF₃ NH-n-Pr CO₂Et 597 OMe CF₃ NHAll CO₂Et 598 OMe CF₃ NH(CH₂)₂O—Me CO₂Et 599 OMe CF₃ N═CH—NMe₂ CO₂Et 600 OMe CF₃ NMe₂ H 601 OMe CF₃ N(Me)Et H 602 OMe CF₃ N(Me)-n-Pr H 603 OMe CF₃ N(Me)All H 604 OMe CF₃ N(Me)(CH₂)₂O—Me H 605 OMe CF₃ NMe₂ CO₂Me 606 OMe CF₃ N(Me)Et CO₂Me 607 OMe CF₃ N(Me)-n-Pr CO₂Me 608 OMe CF₃ N(Me)All CO₂Me 609 OMe CF₃ N(Me)(CH₂)₂O—Me CO₂Me 610 OMe CF₃ NMe₂ CO₂Et 611 OMe CF₃ N(Me)Et CO₂Et 612 OMe CF₃ N(Me)-n-Pr CO₂Et 613 OMe CF₃ N(Me)All CO₂Et 614 OMe CF₃ N(Me)(CH₂)₂O—Me CO₂Et 615 OMe Cl NH₂ H 8.24 (s, 1H), 7.15 (d, 1H), 6.76 (d, 1H), 4.38 (br, 2H), 3.75 (s, 3H), 2.75-2.82 (m, 1H), 1.30-1.38 (m, 2H), 1.20-1.30 (m, 2H) 616 OMe Cl NHMe H 8.22 (s, 1H), 7.15 (d, 1H), 6.80 (d, 1H), 3.70 (s, 3H), 3.05 (s, 3H), 2.75-2.82 (m, 1H), 1.30-1.38 (m, 2H), 1.20-1.30 (m, 2H) 617 OMe Cl NHEt H 618 OMe Cl NH-n-Pr H 619 OMe Cl NHAll H 620 OMe Cl NH(CH₂)₂O—Me H 621 OMe Cl N═CH—NMe₂ H 7.42 (s, 1H), 7.12 (s,1H), 7.05 (d, 1H), 3.75 (s, 3H), 2.85 (s, 6H), 2.0-2.10 (s, 1H), 0.95-1.0 (m, 2H), 0.65-0.70 (m, 2H) 622 OMe Cl NH₂ CO₂Me 623 OMe Cl NHMe CO₂Me 624 OMe Cl NHEt CO₂Me 625 OMe Cl NH-n-Pr CO₂Me 626 OMe Cl NHAll CO₂Me 627 OMe Cl NH(CH₂)₂O—Me CO₂Me 628 OMe Cl N═CH—NMe₂ CO₂Me 629 OMe Cl NH₂ CO₂Et 630 OMe Cl NHMe CO₂Et 631 OMe Cl NHEt CO₂Et 632 OMe Cl NH-n-Pr CO₂Et 633 OMe Cl NHAll CO₂Et 634 OMe Cl NH(CH₂)₂O—Me CO₂Et 635 OMe Cl N═CH—NMe₂ CO₂Et 636 OMe Cl NMe₂ H 8.22 (s, 1H), 7.20 (d, 1H), 7.05 (d, 1H), 3.68 (s, 3H), 2.92 (s, 6H), 2.75-2.80 (m, 1H), 1.30-1.38 (m, 2H), 1.20-1.30 (m, 2H) 637 OMe Cl N(Me)Et H 638 OMe Cl N(Me)-n-Pr H 639 OMe Cl N(Me)All H 640 OMe Cl N(Me)(CH₂)₂O—Me H 641 OMe Cl NMe₂ CO₂Me 642 OMe Cl N(Me)Et CO₂Me 643 OMe Cl N(Me)-n-Pr CO₂Me 644 OMe Cl N(Me)All CO₂Me 645 OMe Cl N(Me)(CH₂)₂O—Me CO₂Me 646 OMe Cl NMe₂ CO₂Et 647 OMe Cl N(Me)Et CO₂Et 648 OMe Cl N(Me)-n-Pr CO₂Et 649 OMe Cl N(Me)All CO₂Et 650 OMe Cl N(Me)(CH₂)₂O—Me CO₂Et

B. FORMULATION EXAMPLES

-   -   a) A dust is obtained by mixing 10 parts by weight of a compound         of the formula (I) and/or its salts and 90 parts by weight of         talc as inert substance and comminuting the mixture in a hammer         mill.     -   b) A wettable powder which is readily dispersible in water is         obtained by mixing 25 parts by weight of a compound of the         formula (I) and/or its salts, 64 parts by weight of         kaolin-containing quartz as inert substance, 10 parts by weight         of potassium lignosulfonate and 1 part by weight of sodium         oleoylmethyltaurinate as wetter and dispersant, and grinding the         mixture in a pinned-disk mill.     -   c) A dispersion concentrate which is readily dispersible in         water is obtained by mixing 20 parts by weight of a compound of         the formula (I) and/or its salts with 6 parts by weight of         alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight         of isotridecanol polyglycol ether (8 EO) and 71 parts by weight         of paraffinic mineral oil (boiling range for example         approximately 255 up to over 277° C.) and grinding the mixture         in a bowl mill to a fineness of below 5 microns.     -   d) An emulsifiable concentrate is obtained from 15 parts by         weight of a compound of the formula (I) and/or its salts, 75         parts by weight of cyclohexanone as solvent and 10 parts by         weight of oxethylated nonylphenol as emulsifier.     -   e) Water-dispersible granules are obtained by mixing         -   75 parts by weight of a compound of the formula (I) and/or             its salts,         -   10 parts by weight of calcium lignosulfonate,         -   5 parts by weight of sodium lauryl sulfate,         -   3 parts by weight of polyvinyl alcohol and         -   7 parts by weight of kaolin,         -   grinding the mixture in a pinned-disk mill and granulating             the powder in a fluidized bed by spraying on water as             granulation liquid.     -   f) Water-dispersible granules are also obtained by homogenizing         and precomminuting, in a colloid mill,         -   25 parts by weight of a compound of the formula (I) and/or             its salts,         -   5 parts by weight of sodium             2,2′-dinaphthylmethane-6,6′-disulfonate,         -   2 parts by weight of sodium oleoylmethyltaurinate,         -   1 part by weight of polyvinyl alcohol,         -   17 parts by weight of calcium carbonate and         -   50 parts by weight of water         -   subsequently grinding the mixture in a bead mill, and             atomizing and drying the resulting suspension in a spray             tower by means of a single-substance nozzle.

C. BIOLOGICAL EXAMPLES

1. Herbicidal Pre-Emergence Effect Against Harmful Plants

Seeds of monocotyledonous or dicotyledonous weeds or crop plants are placed in sandy loam soil in wood-fiber pots and covered with soil. The compounds according to the invention, formulated in the form of wettable powders (WP) or emulsion concentrates (EC), are then applied to the surface of the soil cover in the form of an aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted), with addition of 0.2% wetter. After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants. The damage to the test plants is scored visually in comparison with untreated controls after an experimental time of 3 weeks has elapsed (herbicidal activity in percent (%): 100% activity=plants have died, 0% activity=like control plants). In this context, for example the compounds Nos. 543, 564, 616 and 621 show in each case at least 90% activity against Abutilon theophrasti, Amaranthus retroflexus and Echinochloa crus galli at an application rate of 320 g/ha. Compounds Nos. 4 and 564 show in each case at least 90% activity against Setaria viridis and Stellaria media at an application rate of 320 g/ha.

2. Herbicidal Post-Emergence Activity Against Harmful Plants

Seeds of monocotyledonous or dicotyledonous weeds or crop plants are placed in sandy loam soil in wood-fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the one-leaf stage. The compounds according to the invention, formulated in the form of wettable powders (WP) or emulsion concentrates (EC), are then sprayed on to the green plant parts in the form of an aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted), with addition of 0.2% wetter. After the test plants have been left to stand under optimal growth conditions in the greenhouse for approximately 3 weeks, the activity of the preparations is scored visually in comparison with untreated controls (herbicidal activity in percent (%): 100% activity=plants have died, 0% activity=like control plants). In this context, for example the compounds Nos. 4 and 564 show in each case at least 80% activity against Setaria viridis, Stellaria media and Viola tricolor at an application rate of 80 g/ha. Compounds Nos. 616 and 621 show in each case at least 90% activity against Abutilon theophrasti, Amaranthus retroflexus and Echinochloa crus galli at an application rate of 80 g/ha. 

1. A 4-(3-aminobenzoyl)-5-cyclopropylisoxazole of the formula (I) and/or a salt thereof

wherein A is NR¹R² or N═CR³NR⁴R⁵, R¹ and R² independently of one another are hydrogen, (C₁-C₆)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where the six abovementioned radicals are substituted by m halogen atoms, R³, R⁴ and R⁵ independently of one another are hydrogen, (C₁-C₆)-alkyl or (C₃-C₆)-cycloalkyl, where the three last-mentioned radicals are substituted by m halogen atoms, X and Y independently of one another are hydrogen, (C₁-C₆)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, halogen, (C₁-C₄)-alkyl-S(O)_(n), (C₃-C₆)-cycloalkyl-S(O)_(n), nitro or cyano, Z is hydrogen or CO₂R⁶, R⁶ is (C₁-C₆)-alkyl or (C₃-C₆)-cycloalkyl, m is 0,1, 2, 3, 4 or 5, and n is 0, 1 or
 2. 2. A 4-(3-aminobenzoyl)-5-cyclopropylisoxazole and/or salt as claimed in claim 1, wherein A is NR¹R² or N═CR³NR⁴R⁵, R¹ and R² independently of one another are hydrogen, (C₁-C₆)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R³, R⁴, R⁵ independently of one another are hydrogen or (C₁-C₆)-alkyl, X and Y independently of one another are methyl, methoxy, trifluoromethyl, chlorine, bromine, fluorine or methylsulfonyl, Z is hydrogen or CO₂R⁶, and R⁶ is methyl or ethyl.
 3. A 4-(3-aminobenzoyl)-5-cyclopropylisoxazole as claimed in claim 1, wherein A is NR¹R² or N═CR³NR⁴R⁵, R¹ and R² independently of one another are hydrogen, methyl, ethyl, propyl, methoxyethyl, ethoxyethyl or methoxypropyl, R³, R⁴, R⁵ independently of one another are hydrogen or methyl, X and Y independently of one another are methyl, methoxy, trifluoromethyl, chlorine, bromine, fluorine or methylsulfonyl, Z is hydrogen or CO₂R⁶, and R⁶ is methyl or ethyl.
 4. A herbicidal composition, comprising a herbicidally active content of at least one compound of the formula (I) and/or salt as claimed in claim
 1. 5. The herbicidal composition as claimed in claim 4 comprising a mixture with at least one formulation auxiliary.
 6. A method of controlling undesired plants, comprising applying an effective amount of at least one compound of the formula (I) and/or salt as claimed in claim 1 to a plant and/or to a location of undesired plant growth.
 7. A herbicidal composition as claimed in claim 4 for controlling undesired plants.
 8. A composition as claimed in claim 7, wherein the compound of the formula (I) and/or salt is capable of being employed for controlling undesired plants in crops of useful plants.
 9. A composition as claimed in claim 8, wherein the useful plants are transgenic useful plants.
 10. A compound of the formula (II)

wherein, A is NR¹R² or N═CR³NR⁴R⁵, R¹ and R² independently of one another are hydrogen, (C₁-C₆)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where the six abovementioned radicals are substituted by m halogen atoms, R³, R⁴ and R⁵ independently of one another are hydrogen, (C₁-C₆)-alkyl or (C₃-C₆)-cycloalkyl, where the three last-mentioned radicals are substituted by m halogen atoms, X and Y independently of one another are hydrogen, (C₁-C₆)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, halogen, (C₁-C₄)-alkyl-S(O)_(n), (C₃-C₆)-cycloalkyl-S(O)_(n), nitro or cyano, m is 0,1, 2, 3, 4 or 5, and n is 0, 1 or 2 and L is ethoxy or dimethylamino.
 11. A compound of the formula (IIa)

wherein A is NR¹R² or N═CR³NR⁴R⁵, R¹ and R² independently of one another are hydrogen, (C₁-C₆)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, where the six abovementioned radicals are substituted by m halogen atoms, R³, R⁴ and R⁵ independently of one another are hydrogen, (C₁-C₆)-alkyl or (C₃-C₆)-cycloalkyl, where the three last-mentioned radicals are substituted by m halogen atoms, X and Y independently of one another are hydrogen, (C₁-C₆)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, halogen, (C₁-C₄)-alkyl-S(O)_(n), (C₃-C₆)-cycloalkyl-S(O)_(n), nitro or cyano, Z is hydrogen or CO₂R⁶, R⁶ is (C₁-C₆)-alkyl or (C₃-C₆)-cycloalkyl, m is 0,1, 2, 3, 4 or 5, and n is 0, 1 or
 2. 12. A herbicidal composition comprising at least one compound of claim
 2. 13. A herbicidal composition comprising at least one compound of claim
 3. 14. A method for controlling undesired plants comprising applying an effective amount of at least one compound of claim 2 to plant and/or to a location of undesired plant growth.
 15. A method for controlling undesired plants comprising applying an effective amount of at least one compound of claim 3 to a plant and/or to a location of undesired plant growth. 